Diisopropylethylamine → 1-(9H-fluoren-9-yl)methyl 5-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

HRID 57604

Reaction equation

HRID 57604 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:2]12.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31](ON3C(=O)CCC3=O)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[N:1]1([C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])[CH2:5][CH2:4][CH:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:2]12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 225622051,1-Dimethylethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 711137921-(9H-fluoren-9-yl)methyl 5-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (424 mg, 2 mmol), N-(9-fluorenylmethoxycarbonyloxy) succinimide (600 mg, 1.8 mmol) and DIPEA (310 mg, 2.4 mmol) in dioxane (20 mL) was stirred at room temperature overnight and then concentrated in vacuo. The residue was treated with EtOAc/H2O, separated, and the aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound. MS (m/z): 355 (M-boc+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with EtOAc/H2O
  3. customseparated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bbb159d6afb54307a9d3653fb4fcc415
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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